The town of Montaione is in the province of Florence, but it is at an equal distance from all the most important cities in Tuscany. It is sete at 342 m. of altitude and it has a population of 3,400 inhabitants.

It is possible to visit the Oratory of San Biagio and the XIII-century church of San Regolo in the town of Montaione. Moreover, the area of the Sacro Monte also called the Jerusalem of Tuscany rises near the town. It is a group of temples and chapels raised by Brother Thomas where the Stations of the Cross are represented in earthenware. The origins of the town are lost in legend. It is said that the young man Ajone founded it after he married a young girl who had freed a robber. Actually, the territory has been inhabited since the Roman-Etruscan times and that it became part of Lucca's Lombard Dukedom in 572 A.D. after the Barbarian invasions. One of the last dukes was called Allone and it is highly probable that the place name "Mons Allonis", which is cited in a document dating to 988 and that indicated the relief on which Allone would have risen later, stemmed from it.
In 1118, the Romanesque parish of San Regolo was built. Until the half of the XIII century, Montaione was one of the towns within the jurisdiction of San Miniato. Morever, still in the XIII century, the manufacture of glass developed in the area and the glassmakers of Montaione have been an example in this activity for centuries. Around 1268, Montaione rebelled and decided to annex to the town of San Gimignano, but to get definitively free from the seigniory of San Miniato it had to enter the vast dominions of the Florentine countryside. Therefore, it submitted to the Tuscan regional capital in 1369. In 1395, Montaione paid its new status with the destruction of the castle of Castelalfi that later the Pisans fortified in the frame of their battle against Florence.
At the half of the XV century, Montaione became a pilgrimage destination thanks to the figure of San Vivaldo da San Gimignano, a hermit monk who lived between the XIII and the XIV centuries. According to the legend, the tree inside which his body was found was totally taken by storm by fanatics looking for his relics to the point that it disappeared. Later, an oratory was raised on its roots. It was enlarged in 1416 and rebuilt in 1426 and it was given to the Franciscans at the end of the century.
The XV century also marked the arrival of the dynasty of the Counts of Filicaja who dominated the Montaione until 1800 and in the XIX century it also participated to the process of development of the area through donations, the creation of the electric network and through experiments of agricultural mechanization. In the Second World War, Montaione was involved in the process of industrialization.